Conclusions
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1.
Nitroxyl radicals of derivatives of 3-imidazoline-3-oxide and 3-imidazoline in solutions of strong or superstrong acids undergo reversible disproportionation to form dications: oxoammonium salts protonated at the nitronium or imino group, and diprotonated hydroxylamino derivatives. The stability of the oxoammonium salts and the hydroxylamino derivatives depends both on the structure of the initial radical and on the acid used.
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2.
The radical cations that are present in the equilibrium mixture in concentrations from fractions to several percent are protonated only on the nitronium or imino group.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2277–2283, October, 1986.
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Grigor'ev, I.A., Shchukin, G.I. & Volodarskii, L.B. EPR and1H and13C NMR study of nitroxyl radical conversions in strong and superstrong acids. Russ Chem Bull 35, 2081–2086 (1986). https://doi.org/10.1007/BF00957529
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DOI: https://doi.org/10.1007/BF00957529